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Volumn 38, Issue 17, 1995, Pages 3313-3331

Phosphinic Acid Analogues of GABA. 2. Selective, Orally Active GABAB Antagonists

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYSACLOFEN; 3 AMINOPROPANEPHOSPHINIC ACID; 3 AMINOPROPYL(BUTYL)PHOSPHINIC ACID; 3 AMINOPROPYL(DIETHOXYMETHYL)PHOSPHINIC ACID; 3 AMINOPROPYL(ETHYL)PHOSPHINIC ACID; 3 AMINOPROPYL(METHYL)PHOSPHINIC ACID; 3 AMINOPROPYLBUTYLPHOSPHINIC ACID; 4 AMINOBUTYRIC ACID B RECEPTOR; 4 AMINOBUTYRIC ACID B RECEPTOR BLOCKING AGENT; 4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; 5 HYDROXYTRYPTOPHAN; 5,7 DICHLOROKYNURENIC ACID; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; BACLOFEN; CGP 36216; CLONIDINE; CYCLOHEXYLADENOSINE; DOXEPIN; FLUNITRAZEPAM; GABOXADOL; GLUTAMIC ACID; GRANISETRON; KAINIC ACID; KETANSERIN; MUSCIMOL; NALOXONE; PHACLOFEN; PHOSPHINIC ACID DERIVATIVE; PRAZOSIN; QUINUCLIDINYL BENZILATE; RECEPTOR SUBTYPE; SACLOFEN; SUBSTANCE P; TIOTIDINE; UNCLASSIFIED DRUG;

EID: 0029165253     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00017a016     Document Type: Article
Times cited : (212)

References (79)
  • 2
    • 0019395276 scopus 로고
    • 3H-GABA bind to bicuculline insensitive GABAb sites in rat brain
    • 3H-GABA bind to bicuculline insensitive GABAb sites in rat brain. Nature (London) 1981, 290, 149-152.
    • (1981) Nature (London) , vol.290 , pp. 149-152
    • Hill, D.R.1    Bowery, N.G.2
  • 3
  • 6
    • 0024971897 scopus 로고
    • Antagonism at GABAb receptors by saclofen and related sulphonic analogues of baclofen and GABA
    • Kerr, D. I. B.; Ong, J.; Johnston, G. A. R.; Abbenante, J.; Prager, R. H. Antagonism at GABAb receptors by saclofen and related sulphonic analogues of baclofen and GABA. Neurosci. Lett. 1989, 107, 239-244.
    • (1989) Neurosci. Lett. , vol.107 , pp. 239-244
    • Kerr, D.I.B.1    Ong, J.2    Johnston, G.A.R.3    Abbenante, J.4    Prager, R.H.5
  • 7
    • 0002454146 scopus 로고
    • Potential GABAb receptor Antagonists. VI. The Synthesis of Saclofen and Other Sulfonic Acid Derivatives
    • Abbenante, G.; Prager, R. H. Potential GABAb receptor Antagonists. VI. The Synthesis of Saclofen and Other Sulfonic Acid Derivatives. Aust. J. Chem. 1992, 45, 1801-1810.
    • (1992) Aust. J. Chem. , vol.45 , pp. 1801-1810
    • Abbenante, G.1    Prager, R.H.2
  • 8
    • 0023682435 scopus 로고
    • 2-Hydroxy-saclofen: an improved antagonist at central and peripheral GABAb receptors
    • Kerr, D. I. B.; Ong, J.; Johnston, G. A. R.; Abbenante, J.; Prager, R. H. 2-Hydroxy-saclofen: an improved antagonist at central and peripheral GABAb receptors. Neurosci. Lett. 1988, 92, 92-96.
    • (1988) Neurosci. Lett. , vol.92 , pp. 92-96
    • Kerr, D.I.B.1    Ong, J.2    Johnston, G.A.R.3    Abbenante, J.4    Prager, R.H.5
  • 10
    • 84970551367 scopus 로고
    • Potential GABAb Antagonists. V. The Application of Radical Additions to Styrenes to produce 2-Hydroxysaclofen
    • Abbenante, G.; Prager, R. H. Potential GABAb Antagonists. V. The Application of Radical Additions to Styrenes to produce 2-Hydroxysaclofen. Aust. J. Chem. 1992, 45, 1791-1800.
    • (1992) Aust. J. Chem. , vol.45 , pp. 1791-1800
    • Abbenante, G.1    Prager, R.H.2
  • 11
    • 0023258021 scopus 로고
    • Synthesis and Pharmacological Evaluation of y-Aminobutyric Acid Analogues. New Ligand for GABAb Sites
    • Berthelot, P.; Vaccher, C.; Musadad, A.; Flouquet, N.; Debaert, M.; Luyckx, M. Synthesis and Pharmacological Evaluation of y-Aminobutyric Acid Analogues. New Ligand for GABAb Sites. J. Med. Chem. 1987, 30, 743-746.
    • (1987) J. Med. Chem. , vol.30 , pp. 743-746
    • Berthelot, P.1    Vaccher, C.2    Musadad, A.3    Flouquet, N.4    Debaert, M.5    Luyckx, M.6
  • 12
    • 0024392101 scopus 로고
    • Benzofuran analogues of baclofen: a new class of central and peripheral GABAB-receptor antagonists
    • Kerr, D. I. B.; Ong, J.; Johnston, G. A. R.; Berthelot, P.; Debaert, M.; Vaccher, C. Benzofuran analogues of baclofen: a new class of central and peripheral GABAB-receptor antagonists. Eur. J. Pharmacol. 1989, 164, 361-364.
    • (1989) Eur. J. Pharmacol. , vol.164 , pp. 361-364
    • Kerr, D.I.B.1    Ong, J.2    Johnston, G.A.R.3    Berthelot, P.4    Debaert, M.5    Vaccher, C.6
  • 13
    • 0024509783 scopus 로고
    • Baclofen antagonism by 4-amino-3-(5-methoxybenzo[b]furan2-yl) butanoic acid in the cat spinal cord
    • Beattie, D. T.; Curtis, D. R.; Debaert, M.; Vaccher, C.; Berthelot, P. Baclofen antagonism by 4-amino-3-(5-methoxybenzo[b]furan2-yl) butanoic acid in the cat spinal cord. Neurosci. Lett. 1989, 100, 292-294.
    • (1989) Neurosci. Lett. , vol.100 , pp. 292-294
    • Beattie, D.T.1    Curtis, D.R.2    Debaert, M.3    Vaccher, C.4    Berthelot, P.5
  • 15
    • 84970626637 scopus 로고
    • Organophosphorus Intermediates. VI. The Acid-Catalysed Reaction of Trialkyl Orthoformates with Phosphinic Acid
    • Gallagher, M. J.; Honegger, H. Organophosphorus Intermediates. VI. The Acid-Catalysed Reaction of Trialkyl Orthoformates with Phosphinic Acid. Aust. J. Chem. 1980, 33, 287-294.
    • (1980) Aust. J. Chem. , vol.33 , pp. 287-294
    • Gallagher, M.J.1    Honegger, H.2
  • 17
    • 0001014261 scopus 로고
    • Synthesis of γ-aminopropyl-phosphonous acids using hypophosphorous acid synthons
    • Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G.; Jack, J. Synthesis of γ-aminopropyl-phosphonous acids using hypophosphorous acid synthons. Phosphorus Sulfur 1987, 30, 571-574.
    • (1987) Phosphorus Sulfur , vol.30 , pp. 571-574
    • Dingwall, J.G.1    Ehrenfreund, J.2    Hall, R.G.3    Jack, J.4
  • 18
    • 0001703033 scopus 로고
    • Diethoxymethylphosphonites and Phosphinates. Intermediates for the synthesis of α, β and γ-aminoalkylphosphonous acids
    • Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G. Diethoxymethylphosphonites and Phosphinates. Intermediates for the synthesis of α, β and γ-aminoalkylphosphonous acids. Tetrahedron 1989, 45, 3787-3808.
    • (1989) Tetrahedron , vol.45 , pp. 3787-3808
    • Dingwall, J.G.1    Ehrenfreund, J.2    Hall, R.G.3
  • 19
    • 17244370580 scopus 로고
    • Organic Phosphorus Compounds 101. Preparation and Physical Properties of Bis (aminoalkyl) phosphinic Acids
    • Maier, L. Organic Phosphorus Compounds 101. Preparation and Physical Properties of Bis (aminoalkyl) phosphinic Acids. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 66, 67-72.
    • (1992) Phosphorus, Sulfur Silicon Relat. Elem. , vol.66 , pp. 67-72
    • Maier, L.1
  • 20
    • 84949354260 scopus 로고
    • Organic Phosphorus Compounds 87: Some Reactions of O-Ethyl-2-chloroethylphosphonite
    • Maier, L.; Diel, P. J. Organic Phosphorus Compounds 87: Some Reactions of O-Ethyl-2-chloroethylphosphonite. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 45, 165-176.
    • (1989) Phosphorus, Sulfur Silicon Relat. Elem. , vol.45 , pp. 165-176
    • Maier, L.1    Diel, P.J.2
  • 21
    • 33845283356 scopus 로고
    • Cyanide as an Efficient and Mild Catalyst in the Aminolysis of Esters
    • Hoegberg, T.; Stroem, P.; Ebner, M.; Raemsby, S. Cyanide as an Efficient and Mild Catalyst in the Aminolysis of Esters. J. Org. Chem. 1987, 52, 2033-2036.
    • (1987) J. Org. Chem. , vol.52 , pp. 2033-2036
    • Hoegberg, T.1    Stroem, P.2    Ebner, M.3    Raemsby, S.4
  • 22
    • 0001674348 scopus 로고
    • Osmium-Catalyzed Vicinal Oxyamination of Olefins by N-Chloro-N-argentocarbamates
    • Herranz, E.; Biller, S. A.; Sharpless, K. B. Osmium-Catalyzed Vicinal Oxyamination of Olefins by N-Chloro-N-argentocarbamates. J. Am. Chem. Soc. 1978, 100, 3596-3598.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 3596-3598
    • Herranz, E.1    Biller, S.A.2    Sharpless, K.B.3
  • 23
    • 0000507666 scopus 로고
    • An efficient synthesis of γ-Amino-β-ketoalkylphosphonates from α-Amino acids
    • Chakravarty, P. K.; Combs, P.; Roth, A.; Greenlee, W. J. An efficient synthesis of γ-Amino-β-ketoalkylphosphonates from α-Amino acids. Tetrahedron Lett. 1987, 28, 611-612.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 611-612
    • Chakravarty, P.K.1    Combs, P.2    Roth, A.3    Greenlee, W.J.4
  • 25
    • 0027933763 scopus 로고
    • Locating ligand-binding sites in 7TM receptors by protein engineering
    • Schwartz, T. W. Locating ligand-binding sites in 7TM receptors by protein engineering. Curr. Opin. Biotechnol. 1994, 5, 434-444.
    • (1994) Curr. Opin. Biotechnol. , vol.5 , pp. 434-444
    • Schwartz, T.W.1
  • 26
    • 0026750864 scopus 로고
    • Comparison of the Actions of Baclofen at pre-and postsynaptic receptors in the rat hippocampus in vitro
    • Thompson, S. M.; Gaehwiler, B. H. Comparison of the Actions of Baclofen at pre-and postsynaptic receptors in the rat hippocampus in vitro. J. Physiol. (London) 1992, 451, 329-345.
    • (1992) J. Physiol. (London) , vol.451 , pp. 329-345
    • Thompson, S.M.1    Gaehwiler, B.H.2
  • 33
    • 0001801445 scopus 로고
    • B Receptors and Transmitter Release
    • Bowery, N. G., Bittiger, H., Olpe, H.-R., Eds.; John Wiley & Sons: Chichester
    • B Receptors in Mammalian Function; Bowery, N. G., Bittiger, H., Olpe, H.-R., Eds.; John Wiley & Sons: Chichester 1990; pp 63-80.
    • (1990) B Receptors in Mammalian Function , pp. 63-80
    • Waldmeier, P.C.1    Baumann, P.A.2
  • 37
    • 0026697292 scopus 로고
    • Functional Evidence for Multiple γ-Aminobutyric Acide Receptor Subtypes in the Rat Cerebral Cortex
    • Bonanno, G.; Raiteri, M. Functional Evidence for Multiple γ-Aminobutyric Acide Receptor Subtypes in the Rat Cerebral Cortex. J. Pharmacol. Exp. Ther. 1992, 262, 114-118.
    • (1992) J. Pharmacol. Exp. Ther. , vol.262 , pp. 114-118
    • Bonanno, G.1    Raiteri, M.2
  • 39
    • 0343714807 scopus 로고
    • B Receptor Regulating the Release of Central Neurotransmitters
    • B Receptor Regulating the Release of Central Neurotransmitters. Pharmacol. Commun. 1992, 2, 1-3.
    • (1992) Pharmacol. Commun. , vol.2 , pp. 1-3
    • Raiteri, M.1
  • 41
    • 0023819128 scopus 로고
    • B receptors in the central nervous system
    • B receptors in the central nervous system. Nature (London) 1988, 322, 156-158.
    • (1988) Nature (London) , vol.322 , pp. 156-158
    • Dutar, P.1    Nicoli, R.A.2
  • 42
    • 0023821266 scopus 로고
    • B blocker reduces long-duration inhibition in the neocortex
    • B blocker reduces long-duration inhibition in the neocortex. Eur. J. Pharmacol. 1988, 148, 485-486.
    • (1988) Eur. J. Pharmacol. , vol.148 , pp. 485-486
    • Karlsson, G.1    Pozza, M.2    Olpe, H.-R.3
  • 43
    • 0025924527 scopus 로고
    • B receptors in excitation and inhibition of thalamocortical cells
    • B receptors in excitation and inhibition of thalamocortical cells. Trends Neurosci. 1991, 14, 16-21.
    • (1991) Trends Neurosci. , vol.14 , pp. 16-21
    • Crunelli, V.1    Leresche, N.2
  • 44
    • 0027210947 scopus 로고
    • Blockade of the late inhibitory postsynaptic potential in vivo by the GABAb blocker CGP46381
    • Lingenhoehl, K.; Olpe, H.-R. Blockade of the late inhibitory postsynaptic potential in vivo by the GABAb blocker CGP46381. Pharmacol. Commun. 1993, 3, 49-54.
    • (1993) Pharmacol. Commun. , vol.3 , pp. 49-54
    • Lingenhoehl, K.1    Olpe, H.-R.2
  • 49
    • 0001910430 scopus 로고
    • B Receptor Blocker Improves the Cognitive Performance of Mice, Rats and Rhesus Monkeys
    • B Receptor Blocker Improves the Cognitive Performance of Mice, Rats and Rhesus Monkeys. Pharmacol. Commun. 1992, 2, 93-97.
    • (1992) Pharmacol. Commun. , vol.2 , pp. 93-97
    • Mondadori, C.1    Preiswerk, G.2    Jaekel, J.3
  • 50
    • 0027275243 scopus 로고
    • B Blocker Improves the Cognitive Performance of Mice, Rats, and Rhesus Monkeys
    • B Blocker Improves the Cognitive Performance of Mice, Rats, and Rhesus Monkeys. Behav. Neural Biol. 1993, 60, 62-68.
    • (1993) Behav. Neural Biol. , vol.60 , pp. 62-68
    • Mondadori, C.1    Jaekel, J.2    Preiswerk, G.3
  • 51
    • 0021154364 scopus 로고
    • The effects of various anti-epileptic drugs on e-shock-induced amnesia in mice: dissociability of effects on convulsions and on memory
    • Mondadori, C.; Classen, W. The effects of various anti-epileptic drugs on e-shock-induced amnesia in mice: dissociability of effects on convulsions and on memory. Acta Neurol. Scand. 1984, 69, Suppl. 99, 125-129.
    • (1984) Acta Neurol. Scand. , vol.69 , pp. 125-129
    • Mondadori, C.1    Classen, W.2
  • 52
    • 85022830152 scopus 로고    scopus 로고
    • Manuscript in preparation
    • Mondadori, C.; et al. Manuscript in preparation.
    • Mondadori, C.1
  • 53
    • 0027228004 scopus 로고
    • B receptor binding sites in rat frontal cortex
    • B receptor binding sites in rat frontal cortex. Br. J. Pharmacol. 1993, 110, 724-735.
    • (1993) Br. J. Pharmacol. , vol.110 , pp. 724-735
    • Pratt, G.D.1    Bowery, N.G.2
  • 54
    • 0002552168 scopus 로고
    • B Antagonist CGP36742 Enhances Spatial Learning Performance and Antagonises Baclofen-induced Amnesia in Mice
    • B Antagonist CGP36742 Enhances Spatial Learning Performance and Antagonises Baclofen-induced Amnesia in Mice. Br. J. Pharmacol. 1993, 109 [Suppl.], 74 p.
    • (1993) Br. J. Pharmacol. , vol.109 , pp. 74
    • Carletti, R.1    Libri, V.2    Bowery, N.G.3
  • 55
    • 0026611827 scopus 로고
    • GABAb receptor antagonists: potential new anti-absence drugs
    • Marescaux, C.; Vergnes, M.; Bernasconi, R. GABAb receptor antagonists: potential new anti-absence drugs. J. Neural Transm. 1992, 35 [Suppl.], 179-188.
    • (1992) J. Neural Transm. , vol.35 , pp. 179-188
    • Marescaux, C.1    Vergnes, M.2    Bernasconi, R.3
  • 59
    • 0001952139 scopus 로고
    • GABAb Receptor Mediated Mechanisms in Experimental Absence Seizures in Rat
    • Snead, O. C. GABAb Receptor Mediated Mechanisms in Experimental Absence Seizures in Rat. Pharmacol. Commun. 1992, 2, 63-69.
    • (1992) Pharmacol. Commun. , vol.2 , pp. 63-69
    • Snead, O.C.1
  • 60
    • 0342881141 scopus 로고
    • GABAb Antagonists and AntiAbsence Drugs suppress Gamma-butyrolacone-induced delta waves: A Model for Testing Anti-absence Drugs
    • Klebs, K.; Bittiger, H.; Froestl, W.; Glatt, A.; Hafner, T.; Mickel, S.; Olpe, H.-R.; Schmutz, M. GABAb Antagonists and AntiAbsence Drugs suppress Gamma-butyrolacone-induced delta waves: A Model for Testing Anti-absence Drugs. Pharmacol. Commun. 1992, 2, 171-172.
    • (1992) Pharmacol. Commun. , vol.2 , pp. 171-172
    • Klebs, K.1    Bittiger, H.2    Froestl, W.3    Glatt, A.4    Hafner, T.5    Mickel, S.6    Olpe, H.-R.7    Schmutz, M.8
  • 65
    • 0027331532 scopus 로고
    • GABAb Receptor Antagonists: from Synthesis to Therapeutic Applications
    • Bittiger, H.; Froestl, W.; Mickel, S. J.; Olpe, H.-R. GABAb Receptor Antagonists: from Synthesis to Therapeutic Applications. Trends Pharmacol. Sci. 1993, 14, 391-393.
    • (1993) Trends Pharmacol. Sci. , vol.14 , pp. 391-393
    • Bittiger, H.1    Froestl, W.2    Mickel, S.J.3    Olpe, H.-R.4
  • 67
    • 0002540317 scopus 로고
    • Hydrogenation and Hydrogenolysis. V. Rhodium-Platinum Oxide as a Catalyst for the Hydrogenation of Organic Compounds
    • Nishimura, S. Hydrogenation and Hydrogenolysis. V. Rhodium-Platinum Oxide as a Catalyst for the Hydrogenation of Organic Compounds. Bull. Chem. Soc. Jpn. 1961, 34, 32-36.
    • (1961) Bull. Chem. Soc. Jpn. , vol.34 , pp. 32-36
    • Nishimura, S.1
  • 68
    • 0000497842 scopus 로고
    • Stereochemical Aspects of Ether Oxygen Participation. VII. The Dichotomous Solvolytic Behavior of 4- and 5-Oxocanyl Derivatives
    • Paquette, L. A.; Scott, M. K. Stereochemical Aspects of Ether Oxygen Participation. VII. The Dichotomous Solvolytic Behavior of 4- and 5-Oxocanyl Derivatives. J. Am. Chem. Soc. 1972, 94, 6760-6766.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6760-6766
    • Paquette, L.A.1    Scott, M.K.2
  • 69
    • 0037911009 scopus 로고
    • Convenient Syntheses and Reactions of Two Kinds of Basic α-Dehydroamino Acid Derivatives
    • Shin, C.; Obara, T.; Segami, S.; Yonezawa, Y. Convenient Syntheses and Reactions of Two Kinds of Basic α-Dehydroamino Acid Derivatives. Tetrahedron Lett. 1987, 28, 3827-3830.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3827-3830
    • Shin, C.1    Obara, T.2    Segami, S.3    Yonezawa, Y.4
  • 73
  • 74
    • 0024356397 scopus 로고
    • Metabolism of 3-(p-Chlorophenyl)-pyrrolidine. Structural Effects in Conversion of a Prototype γ-Aminobutyric Acid Prodrug to Lactam and γ-Aminobutyric Acid Type Metabolites
    • Wall, G. M.; Baker, J. K. Metabolism of 3-(p-Chlorophenyl)-pyrrolidine. Structural Effects in Conversion of a Prototype γ-Aminobutyric Acid Prodrug to Lactam and γ-Aminobutyric Acid Type Metabolites. J. Med. Chem. 1989, 32, 1340-1348.
    • (1989) J. Med. Chem. , vol.32 , pp. 1340-1348
    • Wall, G.M.1    Baker, J.K.2


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